Red vs Blue: Building, Attacking, and Defending a Virtual Enterprise Network

Introduction

What happens when you give a team of cybersecurity students the task of building a network, attacking another team's infrastructure, and defending their own? You get a crash course in real-world security operations.

This was our Red vs Blue exercise, a comprehensive cybersecurity project where Team C had to:

  1. Build a complete virtual enterprise network from scratch using Proxmox, VyOS, and pfSense
  2. Deploy security monitoring with Wazuh and Sysmon
  3. Attack a rival team's network to find vulnerabilities (Red Team)
  4. Defend our own infrastructure through monitoring and response (Blue Team)

Team Members: Pranay Garapati, Swarupa Jeedimetla, Dheeraj Kumar Ammineni, Manisharan Chakali, Brahmendra Chowdary Ponduri

Institution: Saint Louis University - Master of Science in Cybersecurity
Project: Week 15 Final Project

Building the Foundation: Network Architecture

Designing Our Network

The first challenge was designing a network that would be both functional and secure. We needed clear boundaries between public and private zones, proper routing, and multiple layers of defense.

Network Diagram Our Team C isolated network architecture - showing the VyOS Router, Ubuntu Server, pfSense Firewall, and Windows 10 Workstation

Here's what we built:

  • VyOS Router - WAN: 203.0.115.2/25, LAN: 178.18.3.1/24 (our edge router)
  • Ubuntu Server - 178.18.3.2/24 (hosting our Wazuh SIEM)
  • pfSense Firewall - WAN: 178.18.3.3/24, LAN: 192.168.102.1/24 (security gateway)
  • Windows 10 - 192.168.102.2/24 (our protected endpoint)

Setting Up Proxmox

We used Proxmox VE 8.4.0 as our virtualization platform. It's powerful, open-source, and perfect for running multiple VMs simultaneously.

Proxmox Login Proxmox VE login screen

Proxmox Dashboard Our Proxmox dashboard showing all VMs - VyOS, pfSense, Ubuntu, and Windows 10 running smoothly

Configuring the Router: VyOS

Getting the router right was crucial. VyOS handles all the routing between our WAN and internal networks, plus NAT for outbound traffic.

The configuration was straightforward but required attention to detail:

  • WAN interface (eth0): 203.0.115.2/25
  • LAN interface (eth1): 178.18.3.1/24
  • DNS servers: 8.8.8.8, 1.1.1.1
  • NAT: Source NAT for outbound traffic

VyOS Connectivity Test Testing VyOS router connectivity - successfully pinging google.com and 8.8.8.8

Once configured, we could ping external servers, which meant our routing was working correctly.

Deploying the Firewall: pfSense

pfSense became our security gateway, protecting the internal network (192.168.102.0/24). It's a powerful firewall with a web-based GUI that makes rule management much easier than command-line alternatives.

pfSense IP Configuration pfSense console showing LAN IP configuration (192.168.102.1/24)

pfSense Web GUI pfSense web GUI showing System Information - version 2.8.0-RELEASE running on QEMU Guest system

The firewall rules were critical. We needed to allow specific traffic while blocking everything else:

pfSense Firewall Rules pfSense LAN firewall rules controlling traffic to ports 22 (SSH), 21 (FTP), 80 (HTTP), and 445 (MS-DS)

Setting Up the Windows Workstation

Our Windows 10 machine needed to be configured as a typical enterprise endpoint. This meant static IP configuration, proper gateway settings, and connectivity testing.

Windows IPv4 Configuration Setting static IP (192.168.102.2) on Windows 10

Windows IP Settings Windows network settings showing IP 192.168.102.2 and gateway 192.168.102.1

Windows IP Verification ipconfig output confirming the static IP configuration

Once configured, we tested connectivity to make sure everything was working:

Windows Connectivity Tests Windows pinging gateway (192.168.102.1), pfSense WAN (178.18.3.3), router (178.18.3.1), and internet (8.8.8.8)

Ubuntu Server: The Security Monitoring Hub

Ubuntu would host our security monitoring infrastructure. Getting the network configuration right here was essential since Wazuh needed to communicate with all endpoints.

Ubuntu Network Configuration Ubuntu terminal showing ip addr flush command to clear old network configuration

Ubuntu Network Testing Configuring Ubuntu interface ens18, setting default gateway, DNS, and testing connectivity to 178.18.3.1, 8.8.8.8, and google.com

Ubuntu Console Work Ubuntu terminal session showing system configuration commands

Security Monitoring: Wazuh & Sysmon

Deploying Wazuh SIEM

Wazuh is an open-source SIEM that collects and analyzes security logs from all endpoints. We deployed it on the Ubuntu server, and it became our central nervous system for security monitoring.

Wazuh Endpoints Wazuh dashboard showing 1 active agent (Windows machine at 192.168.102.2)

Wazuh Dashboard Wazuh agent details - DESKTOP-23M8HBN running Windows 10 Home

To allow Wazuh traffic, we had to configure firewall rules:

pfSense Rules for Wazuh pfSense firewall rules allowing Wazuh traffic on ports 1514-1515

Installing Sysmon on Windows

Sysmon (System Monitor) captures detailed system events on Windows endpoints. It's incredibly powerful for detecting suspicious activity, but getting it configured correctly took some time.

Sysmon Service Check Verifying Sysmon64 service is running on Windows

Sysmon Events Windows Event Viewer showing Sysmon operational logs capturing process creation events

We configured Sysmon using a custom XML configuration file from SwiftOnSecurity's GitHub repository, which provides excellent default rules for detecting common attack techniques.

Sysmon Config GitHub Viewing Sysmon configuration from SwiftOnSecurity GitHub repository

Sysmon XML Content Sysmon XML configuration file content

Seeing Security Events in Real-Time

Once everything was configured, Wazuh began capturing security events in real-time. It was exciting to see the dashboard light up with activity:

Wazuh Security Alerts Wazuh dashboard showing 32 security events with detailed alert information

Hardening Our Systems

Before the Red vs Blue exercise began, we hardened our systems to establish a security baseline. This included:

  • Windows Defender configuration
  • Ubuntu firewall rules
  • Disabling unnecessary services
  • Applying security best practices

Windows Hardening Windows Defender and security hardening configurations

Ubuntu Hardening Ubuntu security hardening settings and firewall configuration

Setting Up WireGuard VPN

For secure remote management, we set up WireGuard VPN. It's fast, modern, and much simpler to configure than traditional VPN solutions.

WireGuard Status WireGuard VPN showing active tunnel with peer connection

VPN Connectivity Test Testing connectivity through the VPN tunnel

Red Team Operations: Attacking the Rival Network

Now for the fun part: attacking a rival team's network (192.168.26.6). As the Red Team, our goal was to identify vulnerabilities and see how far we could get.

Finding 1: SMB Access Achieved

We started with SMB enumeration and quickly discovered we could access multiple shares. This was a significant finding: SMB shares often contain sensitive data.

SMB Enumeration with smbmap Using smbmap tool to enumerate SMB shares on 192.168.26.6 - discovered ADMIN$, C$, F$, IPC$ shares

SMB File Listing Using Impacket smbclient.py to browse and list files within the SMB shares

Finding 2: Testing Target Reachability

Before diving deep, we verified the target was accessible and tested which ports responded:

Connectivity Testing PowerShell connectivity tests showing ping to 192.168.26.6 successful, port 80 open, port 22 closed

Finding 3: IIS Web Server with Default Configuration

The target was running IIS with default settings, a classic mistake. Default configurations are often insecure, and this was no exception.

IIS Default Page Accessing the default IIS "Internet Information Services" welcome page from Kali

Finding 4: Network Service Scanning

Nmap revealed multiple open services that increased the attack surface significantly:

Nmap Port Scan Nmap scan showing multiple open ports on 192.168.26.6

Nmap Service Detection Detailed Nmap service version scan revealing HTTP, NetBIOS, and Microsoft-ds

Finding 5: SMB Brute Force Attempt

We attempted brute force attacks against the SMB service using Metasploit. However, account lockout policies prevented us from gaining access this way:

Metasploit SMB Attack Metasploit smb_login module attempting brute force - all attempts failed due to account lockout

Finding 6: SMB Signing Disabled

This was a critical finding: SMB signing was disabled, which creates a vulnerability to man-in-the-middle attacks:

CrackMapExec Scan CrackMapExec showing SMB signing is disabled (Signing:False)

Finding 7: RPC Information Disclosure

We used rpcclient to extract system information without full authentication. This is a common information disclosure vulnerability:

RPC Enumeration Using rpcclient to query system information via RPC

Finding 8: FTP on Non-Standard Port 123

One of the most interesting findings was an FTP server running on port 123 (typically used for NTP). Security by obscurity doesn't work: we found it anyway.

FTP Access Connecting to FTP on port 123 and downloading files (challenge.zip, john.txt)

We downloaded and analyzed the files:

Downloaded File Analysis Analyzing the downloaded main.c file

Code Content Reviewing the source code content

Blue Team Operations: Defending Our Network

While attacking the rival network, we simultaneously monitored our own infrastructure (192.168.102.2) for threats. This dual perspective was incredibly valuable: we could see both sides of the security equation.

Threat Hunting

We used Wazuh's threat hunting dashboard to actively search for indicators of compromise. This proactive approach helped us catch potential issues early:

Wazuh Threat Hunting Wazuh threat hunting dashboard with multiple detection tabs

Analyzing Security Events

The security events captured by our monitoring system told a story. We saw command shells, SSH failures, and malware detection attempts:

Wazuh Security Events Security events log showing command shells, SSH failures, and malware detection

We dove deep into specific rule detections:

Rule Detection 92307 Detailed analysis of Rule ID 92307 (Service creation detection)

Rule Detection 61605 Detailed analysis of Rule ID 61605

Registry Monitoring Registry modification detection showing service-related changes

MITRE ATT&CK Mapping

One of the most powerful features of Wazuh is its integration with the MITRE ATT&CK framework. We mapped detected events to understand attacker tactics:

MITRE ATT&CK Dashboard Wazuh MITRE ATT&CK view showing detected techniques

We investigated specific MITRE techniques like T1105 (Ingress Tool Transfer):

T1105 Detection Analyzing T1105 - Ingress Tool Transfer technique

T1105 JSON Details Event details in JSON format showing PowerShell execution

T1105 Full Analysis Complete event analysis with process details

T1105 Event Table Event table view showing multiple T1105 detections

Learning Outcomes

This project taught me how to build and secure a full virtual network using Proxmox, VyOS, pfSense, Ubuntu, and Windows. I learned how IPs, gateways, NAT, DNS, and firewall rules must be configured correctly, and how small mistakes can break connectivity.

The Red Team work showed me how attackers use scanning, enumeration, and misconfigurations to gain access, especially through SMB and FTP.

The Blue Team work taught me how Wazuh and Sysmon collect and map events to MITRE ATT&CK, and how defenders detect suspicious behavior.

Troubleshooting network issues, fixing Wazuh agent problems, and working with teammates improved my problem-solving, patience, and communication.

Reflection

This project was challenging but gave me real experience in building, attacking, and defending a network. The first weeks were hardest due to routing and interface issues, but solving them helped me understand the network better.

Connecting the Wazuh agent and getting Sysmon events to appear took the most time, but fixing those problems improved my troubleshooting skills.

On the Red Team side, accessing SMB and FTP showed how simple weaknesses can be exploited. On the Blue Team side, analyzing alerts helped me understand how SOC monitoring works.

Overall, this project made me more confident with tools and improved both my offensive and defensive cybersecurity skills.

Conclusion

This Red vs Blue exercise provided hands-on experience with:

Offensive Skills (Red Team):

  • Network reconnaissance and port scanning
  • SMB enumeration and exploitation
  • Web vulnerability analysis
  • Identifying misconfigurations (FTP on port 123, SMB signing disabled)

Defensive Skills (Blue Team):

  • SIEM deployment and configuration (Wazuh)
  • Endpoint monitoring (Sysmon)
  • Security event analysis
  • MITRE ATT&CK threat intelligence mapping
  • Incident detection and response

Key Lessons:

  1. Default configurations are dangerous - IIS, SMB, and FTP were all vulnerable in their default states
  2. Security by obscurity fails - Moving FTP to port 123 didn't hide it from basic scanning
  3. Monitoring is essential - Without Wazuh and Sysmon, we wouldn't have visibility into attacks
  4. Layered defense works - Multiple security controls (firewall rules, account lockout, monitoring) stopped many attacks

This project simulated real-world security operations and gave us practical experience that directly applies to SOC analyst, penetration tester, and security engineer roles.

Technologies Used

Infrastructure:

  • Proxmox VE 8.4.0 - Virtualization platform
  • VyOS - Software router
  • pfSense 2.8.0 - Firewall and gateway

Operating Systems:

  • Windows 10 Home - Target workstation
  • Ubuntu Server - Security monitoring host
  • Kali Linux - Red Team attack platform

Security Tools:

  • Wazuh - SIEM and log analysis
  • Sysmon - Windows system monitoring
  • MITRE ATT&CK - Threat intelligence framework
  • WireGuard - Secure VPN

Offensive Tools:

  • Nmap - Network scanner
  • Metasploit - Exploitation framework
  • CrackMapExec - Post-exploitation
  • Legion - Network enumeration
  • rpcclient - RPC enumeration
  • smbclient - SMB access

Project completed December 2025 as part of Saint Louis University's Master of Science in Cybersecurity program.